The Story of Outlaw Country in 33 Songs

The story of outlaw country starts in very different places, depending on who is spinning the yarn. Historian Joe Nick Patoski wonders if it all started in 1972, after Willie Nelson’s home outside Nashville caught fire, prompting him to move back to Austin and play dancehalls around Texas. “Outlaws & Armadillos,” the Country Music Hall of Fame’s current exhibition, insists the movement started with Bobby Bare in the 1970s, when the headstrong country star negotiated a new contract with RCA Records that allowed him to produce his own albums; soon, Nelson and Waylon Jennings scored similar deals and made thematically cohesive albums like 1974’s Phases & Stages and 1973’s Honky Tonk Heroes. Or, as Steve Earle recalls—and he’s an expert—the whole affair happened because of Doug Sahm. (More on that in a minute.)

While the locations and players change, what all these origin stories have in common is motivation: The outlaws wanted freedom. The singers wanted to sing the songs they liked, written by people like Guy Clark, Ray Wylie Hubbard, and Billy Joe Shaver, among others. They wanted to record at independent studios like Tompall Glaser’s “Hillbilly Central,” the Nashville hub for pretty much everybody even tangentially associated with the outlaw movement. They wanted to play the dancehalls like Armadillo World Headquarters in Austin, where long-haired hippies and buzzcut rednecks struck a precarious truce to enjoy some good tunes together. In short, they wanted to control their own musical destinies.

Even before the term “outlaw” was popularly used to describe this movement, many of these artists were writing about their lives on the road with sophisticated self-reflection, self-deprecating humor, and desperado pathos. The outlaw lifestyle became their most prominent subject, for better or for worse. Jennings summed it all up with two crucial questions: In 1975, he released his signature hit, “Are You Sure Hank Done It This Way?”—a self-aware consideration of the changing nature of the industry. Three years later, he followed it with “Don’t You Think This Outlaw Bit’s Done Got Out of Hand?” which chronicled the drug busts and break-ups that accompanied the outlaw mantle.

By the late 1970s, the scene was already dying down. Nelson moved out to L.A., even recording an album of standards called Stardust in 1978. Armadillo World Headquarters closed two years later. But while the movement may have sputtered, the animating idea behind it remained powerful well into the ’80s, when the country mainstream made room for twangy eccentrics like k.d. lang and Lyle Lovett, as well as upstarts like Earle, Dwight Yoakam, and Lucinda Williams. In the ’90s, it was largely supplanted by alt-country rebels flipping the bird in the general direction of Nashville; however, in the last 10 years, the outlaw ethos has inspired a new generation of artists such as Miranda Lambert, Jason Isbell, and Sturgill Simpson, who provide a musical—and often political—alternative to the arena country mainstream.

In compiling these 33 representative songs, we’ve tried to keep our definition of “outlaw country” as broad as possible, in order to track many of its phases and stages. Our list, while by no means exhaustive, traces this music’s grit and glory from its contested origins to the present moment, from Texas dancehalls to streaming playlists, from Johnny Cash to Miranda Lambert.

But before we dig into all that, let’s take a moment to check in with a man who has seen every stage of the outlaw movement and lived to tell the tale: Steve Earle. A Texas native who cut his teeth in the Texas outlaw scene before moving to Nashville and learning the ropes from Guy Clark and Townes Van Zandt, he’s released 16 studio albums in the last 30 years—the most recent of which, last year’s So You Wannabe an Outlaw, reconsiders the heroes of his youth.

Last Exit to Nashville: A Conversation With Steve Earle

Pitchfork: You were there at the early days of the Texas outlaw scene. How did that start?

Steve Earle: The outlaw thing happened because of Doug Sahm. Doug, mainly because he couldn’t get Big Red—a bright-red soft drink that tastes like bubblegum—leaves Mill Valley [outside San Francisco] and goes back to Texas. It was Doug who told Willie Nelson he should play Armadillo World Headquarters, and he told [Atlantic president] Jerry Wexler, “If you want progressive country music, you need to sign Willie.” That’s how we got Shotgun Willie and Phases & Stages.

I saw a lot of weirdness and rampant drug and alcohol use in Texas. Not that I didn’t use alcohol and drugs, but it was out of control. I though Nashville would be more serious.

What was Nashville like when you arrived?

When I got there, in November of ’74, the inmates were in charge of the fucking asylum. But it was shocking how few places there were to play, but that actually turned out to be a strength. One place was called Bishop’s Pub, and you could do a set and pass the hat or you could have two beers, but you couldn’t do both. There was a place called the Village, which is still there. Once a month there was the original Nashville writers’ night at the Exit/In. That was really hard to get on.

How did you manage to land that gig?

I got on it because Guy Clark insisted. There was always an established act that closed the night, and he volunteered in order to get me on the show. Since there were so few places to play, any night of the week, we'd be at somebody’s house or in a hotel room, a bunch of people with guitars. We were trying to impress each other with what we’d written—or, mainly, we were trying to impress [Guy Clark’s wife] Susanna.

Coke hadn’t quite hit yet when I got there. When I got there, it was just pot and a lot of alcohol and speed. There was a doctor named Snap, believe it or not, in East Nashville. My initiation was: Somebody took me out to him ’cause I was another person who could have a prescription. There wasn't enough speed to go around to get the songs written. First thing Guy Clark did when he met me was ask me if I had any, because I was so wired up. But I just kinda came like that. That’s one drug I’ve never taken a lot of.

I read that Waylon Jennings wore a special bandana as a show of support while you were in prison in the early 1990s.

That’s one of those things that makes me cry. I’d been furloughed out of jail into a treatment center, and it’s pretty emotional when you’re detoxing. I got letters from my parents and my uncle, but I got three letters from other musicians. I got one from Johnny Cash, I got one from Emmy [Harris], and I got one from Waylon. There wasn’t even a letter, just a letter with a snapshot of him, and on the back of it in his big, huge scrawl, it said, “I’m wearing this bandana for you.” It was a big deal for me.

Steve Earle. Graphic by Martine Ehrhart.

He seems like someone who was very supportive of songwriters, like you and Billy Joe Shaver.

Waylon was complicated. He was pretty hard-headed, but he liked me for some reason, once I got on his radar. He recorded my song “The Devil’s Right Hand” and then later brought it into a Highwaymen session with Johnny, Willie, and Kris [Kristofferson]. I also produced a bonus track for the 20th anniversary of Wanted! The Outlaws [the best-selling 1976 compilation album with Jennings, Nelson, and more]. He did a song of mine called “Nowhere Road,” a duet with Willie. That might have been the last time I saw him. It was only a couple years before he passed away. I was on the road all the time and he was on the road all the time. Then he got sick. He lost a leg. But he kept working right up ’til the end.

A lot of the songs coming out of the outlaw movement seem to be about documenting that scene, that life on the road, like Waylon’s “Are You Sure Hank Done It This Way?”

The part of it that you’re talking about, where it began to document itself, is part of its demise. The worst of all those songs David Allan Coe wrote was “Willie, Waylon, and Me.” I really hate it. And I wrote some of those songs, like “It’s Our Town” and “Little Rock ’N’ Roller.” So I’m not innocent in this, but I didn’t do it on purpose. I didn’t do it because I was smart. I stumbled into it, but I learned a lesson from it.

I remember reading in Country Music magazine, I think it was [the art and music critic] Dave Hickey who wrote about being on an airplane and sitting next to this roughneck coming in from an offshore rig. They got to talking, and he asked Dave what he did. He said, “I write about country music.” That guy says, “Those country singers, they used to sing about us. Now all they do is sing about each other.”

You mentioned you learned a lesson from this. What was it?

You do lose touch with your audience. Johnny Cash told me once, “I really love that song of yours, ‘Little Rock ’N’ Roller.’” About a week later, I was at a truck stop, and this truck driver came up to me and said the same thing. That was when the light went on. The reason they both relate to that song is because they both have kids and they both miss their kids when they’re on the road. That song is still valid because it wasn’t just about people feeling sorry for themselves because they’re riding around on a bus that cost more than most people’s houses. That’s what audiences don’t want to hear.

Who do you think embody some of those outlaw principles these day?

A lot of them are girls. Miranda Lambert’s last record is a fucking masterpiece. Women are being marginalized in country music more than ever, just because bro country thinks it’s such a dude thing. Women are reacting to it and they’re the best songwriters. A lot of it’s Brandy Clark. She’s in the middle of it all and she’s a badass.

“Streets of Baltimore”

1966

Gram Parsons may have made it famous, but “Streets of Baltimore” belongs to Bobby Bare, who first recorded the dramatic tune in 1966. From his album of the same name, “Streets of Baltimore” is a relic of Bare’s first stint on the RCA Victor label, widely regarded to be his breakout period in country music. Lyrically, the Tompball Glaser and Harlan Howards-penned song takes romantic devotion to its heart-wrenching extreme, telling of a man who “sold the farm to take [his] woman where she longed to be,” before getting unceremoniously kicked to the curb. Bare’s tender croon lends the song believable longing and regret, while the otherwise simple arrangement ups the drama with countrypolitan “oohs” and “ahhs.” Bare would go on to work with a laundry list of country artists, including Kris Kristofferson and Rosanne Cash, but “Streets of Baltimore” is a classic look at how he began with a truly outsider spirit: lonely, defiant, and searching for home. –Brittney McKenna

“Folsom Prison Blues” (Live)

1968

“I sat with my pen in my hand, trying to think up the worst reason a person could have for killing another person, and that’s what came to mind.” This is how Johnny Cash explained the pivotal lyric in his signature song: “I shot a man in Reno/Just to watch him die,” sung near the beginning of “Folsom Prison Blues.” Originally appearing on his 1957 debut With His Hot and Blue Guitar, the shuffling, nihilistic prisoner’s anthem was delivered in its definitive form at Folsom in 1968.

Cash’s inimitable voice—both stern and desperate, unbreaking in the face of the inmates’ spontaneous applause—codified how we define the outlaw persona in country. Of course, nothing about “Folsom” is exactly as it seems: The crowd’s roar of approval after he introduces himself was rehearsed; the applause after that infamous lyric was added in post-production; that crucial lyric was possibly inspired by a Leadbelly recording of a traditional murder ballad. Yet, somehow, nothing can alter the song’s dark magic: Cash sings his blues like the gospel. –Sam Sodomsky

“Mendocino”

1969

A childhood prodigy who wore handmade Western suits to play the steel guitar before he even hit puberty, Doug Sahm changed the landscape of the Texas sound—and country music as a whole—with the help of his ace collective, the Sir Douglas Quintet. Breaking through several Lone Star stereotypes, they fused the spirit of psychedelic California with funk, soul, and Tejano, all while paying close attention to the melodies and mod adornments pouring over from the British Invasion (so much so that Dick Clark once asked the band, “Where in England are you guys from?”). Actually hailing from San Antonio but based outside San Francisco, Sahm and crew dug into the rich culture of their home state for “Mendocino,” a radio hit that praised the spirit of West Coast free love while making deep references to Mexican music, and not superficially, either: Sahm was an extremely knowledgeable student of the arts, and could pull as easily from Mexico City’s underground rock as he did its traditional horns. With “Mendocino,” the Quintet proved that country could be just as groovy as the Grateful Dead, and with endless malleability, too. –Marissa R. Moss

“Sunday Mornin’ Comin’ Down”

1970

In the late ’60s, Johnny Cash was the Man in Black and Kris Kristofferson was the Guy With the Broom. Working as a janitor at CBS’ recording studios, the former Army captain, Rhodes scholar, and aspiring literature teacher eavesdropped on Cash’s sessions and went home to write his own songs, with the dream of maybe running in the same circles someday. Soon, he befriended June Carter Cash, who checked out his tapes and played her favorites for Johnny when he got home at night. “That man’s a poet,” Cash responded. “Pity he can’t sing.”

Somewhere along the way, all the rejection led Kristofferson to write the song of his lifetime: a sweeping, broken ballad called “Sunday Mornin’ Comin’ Down.” It was the one that turned Cash into a convert, painting such a stark, unglamorous portrait of a man at the end of his rope that you can’t help but hear yourself in it. When Cash debuted his hit cover, he refused to change a particularly controversial line (“Wishing, lord, that I was stoned”) so as not to lose the integrity of Kristofferson’s message. Since then, a lot of singers have taken it on, but the song remains tethered to Kristofferson’s legacy. As he came to terms with his strengths and limitations—he never really did learn to sing—it remains his unforgettable ode to the trying times behind him and the hope that’s always just around the corner. –Sam Sodomsky

“Me and Paul”

1971

Before Willie Nelson was a national treasure and our collective wise, stoned grandfather, he was a down-and-out kid with a guitar, selling songs around Nashville. His 1971 masterpiece Yesterday’s Wine was somehow already his 13th studio album, and he was pushing 40 by the time of its release. Still, he was far from a household name. Facing career frustrations, a recent divorce, and a burnt-down ranch in Tennessee, he compiled this record of older compositions and heady new, astrologically-linked concept songs that put him even further from the good graces of his label.

Near the end of the album is its stubborn, road-weary highlight, “Me and Paul.” The “Paul” in the title referred to his drummer, Paul English, the backbeat of his band and his reminder to always push onward, in both a musical and spiritual sense. It’s an ode to the travels they’d undertaken together, the unfriendly faces they’d seen along the way and the drive they inspired in each other to fight onward. Unsurprisingly, Yesterday’s Wine would be another commercial failure, but the outlaw anthem at its heart proved prophetic. Willie was receiving his education on the road, and soon America would be learning from him, too. –Sam Sodomsky

“Kentucky”

1972

Sammi Smith begins “Kentucky” pillow-talk quiet, the approach that two years earlier launched her signature hit, a gender-switched version of Kris Kristofferson’s “Help Me Make It Through the Night.” Smith rarely gets mentioned in outlaw country discussions because lush, pop-inclined records like “Help Me…” were countrypolitan exemplars of what the outlaws were presumably fighting. Also not helping her cause: She was a woman in a good-ol’-boys club that fetishized not being tied down and included so few women, you could count them on your cowboy boots. But Smith ran with outlaws from the start. Her tourmate Waylon Jennings dubbed her a “girl hero,” not a “girl singer” as country women were then commonly known, and Willie Nelson booked her for his first Fourth of July Picnic in 1973.

Here, she’s the outlaw—on the road, alone and free—when she hears a man called “Kentucky” sing and falls in love. In real life, this was Kentucky-born Jody Payne, her husband and guitarist for Willie Nelson’s Family Band. In the raucous second verse, which abandons countrypolitan for glorious outlaw-predicting rock and includes more cymbal crashes than any other country record could handle, she and Payne roam from gig to gig together. But Sammi’s singing lead. –David Cantwell

“Pancho and Lefty”

1972

You can’t talk about outlaw country music without talking about “Pancho and Lefty,” one of the genre’s best-loved songs—and you can’t talk about songwriting without paying respect to Townes Van Zandt, one of music’s finest songwriters, genre be damned. Willie Nelson and Merle Haggard’s take on “Pancho and Lefty” may have topped the charts, but it’s Van Zandt’s original—which appeared on his 1972 album The Late Great Townes Van Zandt—that truly captures the complexity of its characters. The storied songwriter follows two Mexican bandits whose relationship is marked by betrayal, ending with Pancho dead at the hands of the federales. (Some folks theorize that Pancho is the real-life bandit Pancho Villa.) With his gently picked guitar and aching vocals, Van Zandt makes the case for the alienation felt by both men, imploring the listener, “Save a few [prayers] for Lefty too.” It cemented Van Zandt’s legend, as he knew; as he introduces the song in the 1981 documentary film Heartworn Highways, “I’ll play a medley of my hit.” –Brittney McKenna

“Dallas”

1972

One of the biggest flops of the outlaw movement eventually became one of its biggest successes. Formed in 1972, the Flatlanders were a strange-even-for-the-’70s band, distinguished by Jimmie Dale Gilmore’s high warble, Steve Wesson’s cosmic singing saw, and an abiding interest in Buddhism. For a year or so, they were one of the most promising groups in the Texas Panhandle, but their first single, a soaring country tune called “Dallas,” went nowhere. It’s a shame, too: Featuring some dusty harmonies and a stately melody that’s both old-school country and new-school outlaw, the song is similar to Gram Parsons’ “Sin City,” minus the moralizing. It depicts the Texas city as the antithesis of both Lubbock and its music scene: Here, the city may look beautiful from a DC-9 at night, but it’s ugly at street level. When “Dallas” failed to burn bright, the Flatlanders were dropped by their label and quietly went their separate ways. But Gilmore, Hancock, and Ely all enjoyed such prominent solo careers in the late 1970s that the Flatlanders became a cult commodity over the next few decades, thanks to Rounder Records’ appropriately titled More a Legend Than a Band. –Stephen Deusner

“I Been to Georgia on a Fast Train”

1973

The pride of Corsicana, Texas, was one of the finest songwriters associated with the outlaw movement, as he depicted country life with humor, wit, and a dusty poetic style. His debut single, “I Been to Georgia on a Fast Train,” off his needs-to-be-reissued Old Five and Dimers Like Me, was covered by Johnny Cash, Emmylou Harris, and…Phish? And Waylon Jennings recorded a full album of Shaver’s tunes, 1973’s epic Honky Tonk Heroes.

With its runaway-train drumbeat and rambling guitar licks, “Georgia” is a sharply defiant and studiously autobiographical tune; in it, he describes his mother leaving him “the day I was born,” his grandmother raising him, and quitting school after eighth grade. However, it doesn’t capture two of the most alarming details of Shaver’s life: He lost a few fingers in a factory accident when he was a young man, and he shot somebody during a bar brawl when he was an old man. Of the latter incident, he described it as only he could: “I hit him right between a mother and a fucker.” –Stephen Deusner

Guacamole

Gary P. Nunn

“London Homesick Blues (Home With the Armadillo)”

1973

Gary P. Nunn had to travel halfway around the world to really appreciate the Lone State State. In the early 1970s, he was playing bass with Michael Murphey, then a rising country star on a major label and a world tour. During a stopover in England, Nunn found himself stuck in a cramped flat with no heat and a cowboy wardrobe that drew jeers from everyone on the street. From this miserable experience he got “London Homesick Blues,” in which he enumerates the joys of Texas: armadillos and good country music, not to mention “the friendliest people and the prettiest women you’ve ever seen.” Armadillos, it should be noted, was a popular nickname for outlaw country fans back in Texas, which makes the song an affectionate anthem for the scene he’d left behind.

Of course it didn’t take long for Nunn to get back home, whereupon he joined Jerry Jeff Walker’s legendary Lost Gonzo Band. Walker put his new bass player on the spot for an unrehearsed performance of “London Homesick Blues” at the Luckenbach Dancehall, and thank god the tapes were rolling. That performance caps Walker’s landmark 1973 live-ish album Viva Terlingua! and eventually became the theme song for “Austin City Limits.” –Stephen Deusner

“Up Against the Wall, Redneck Mother”

1973

The rednecks and the hippies may have found common ground at the Texas dancehalls where Willie and Waylon and Jerry Jeff played, but that doesn’t mean the truce between these two culturally oppositional groups was always easy. In fact, Ray Wylie Hubbard’s signature tune suggests that old tensions and prejudices remained. Born of an errant beer run that put the long-haired Hubbard in a middle-of-nowhere hick bar, “Up Against the Wall, Redneck Mother” pokes fun at both rednecks and their mothers, the latter of whom are responsible for the former “hanging out in honkytonks, just kicking hippies’ asses and raising hell.” Thanks to Jerry Jeff Walker’s rousing cover on his 1973 album Viva Terlingua!, the song became an outlaw standard, albeit one that Hubbard still finds a little embarrassing. “The way I this song is, this song probably shoulda never been written, let alone recorded, let alone recorded again,” he stated in a 1998 live performance. “I feel bad about it, except twice a year I go out to my mailbox. I get a letter and there’s a check in it, and by God, it ain’t that bad.” –Stephen Deusner